Not sure what to wear with high waisted shorts? The easiest way to wear high-waisted shorts is to pair them with a plain tank or a crop top, flat sandals and some cute accessories. Or go for a boho look with a loose tank and super long sweater. Or maybe use them as a sort of beach cover-up. Pair them with a cute swimsuit when you’re hanging by the pool or beach. The high-rise jean short is truly a summer staple!